CHEBI:15638 - (6R)-5,10-methenyltetrahydrofolic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (6R)-5,10-methenyltetrahydrofolic acid
ChEBI ASCII Name (6R)-5,10-methenyltetrahydrofolic acid
Definition The 5,10-methenyl derivative of tetrahydrofolic acid arising from enzymatic cyclisation of 5-formyltetrahydrofolic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:12069, CHEBI:12068, CHEBI:1987
Supplier Information
Download Molfile XML SDF
Formula C20H22N7O6
Net Charge +1
Average Mass 456.43226
Monoisotopic Mass 456.16261
InChI InChI=1S/C20H21N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/p+1/t12-,13+/m1/s1
SMILES [H][C@]12CNc3nc(N)[nH]c(=O)c3[N+]1=CN(C2)c1ccc(cc1)C(=O)N[C@@H](CCC(O)=O)C(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
water-soluble vitamin (role)
Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine.
(via B vitamin )
Application(s): nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
(via B vitamin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (6R)-5,10-methenyltetrahydrofolic acid (CHEBI:15638) has functional parent (6R)-5,10-methylenetetrahydrofolic acid (CHEBI:1989)
(6R)-5,10-methenyltetrahydrofolic acid (CHEBI:15638) has role Escherichia coli metabolite (CHEBI:76971)
(6R)-5,10-methenyltetrahydrofolic acid (CHEBI:15638) has role mouse metabolite (CHEBI:75771)
(6R)-5,10-methenyltetrahydrofolic acid (CHEBI:15638) is a methylenetetrahydrofolic acid (CHEBI:25297)
(6R)-5,10-methenyltetrahydrofolic acid (CHEBI:15638) is conjugate acid of (6R)-5,10-methenyltetrahydrofolate (CHEBI:57455)
Incoming (6R)-5,10-methenyltetrahydrofolate (CHEBI:57455) is conjugate base of (6R)-5,10-methenyltetrahydrofolic acid (CHEBI:15638)
N-{4-[(6aR)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydro-8H-imidazo[1,5-f]pteridin-10-ium-8-yl]benzoyl}-L-glutamic acid
Synonyms Sources
(6R)-5,10-CH+-H4folate JCBN
5,10-Methenyltetrahydrofolate KEGG COMPOUND
5,10-methenyltetrahydropteroylglutamate ChemIDplus
Anhydroleucovorin ChemIDplus
Manual Xrefs Databases
C00019687 KNApSAcK
View more database links
Registry Numbers Types Sources
6184059 Beilstein Registry Number Beilstein
7444-29-3 CAS Registry Number ChemIDplus
Last Modified
27 January 2016
General Comment
2004-01-09 The naturally occurring compound is the tetrahydrofolate 6R stereoisomer.